ISSN:
0009-2940
Keywords:
Mesoionic compounds
;
Tetrazolium salts, 1,3-diaryl-
;
Carbenes, mesoionic
;
Carbene-metal complexes
;
Nucleophilic substitution
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1,3-Diaryltetrazolium salts 5 and 6 have been prepared by nitric acid oxidation of the corresponding 5-thiolates 4. The reaction of 5 with mercury(II) acetate gives (1,3-diaryltetrazolylene)mercury(II) complexes 7, which provide 5-halotetrazolium salts 8 - 10 by treatment with halogen. 1,3-Diphenyltetrazolylene (16), generated in situ by proton abstraction of 1,3-diphenyltetrazolium salts 5a or 6a, has been trapped with p-(dimethylamino)benzenediazonium tetrafluoroborate to form 18/18′. The palladium(II) complex 19 of 1,3-diphenyltetrazolylene has been prepared by oxidative addition of tetrakis(triphenylphosphane)palladium(0) to 5-chlorotetrazolium salt 8. The reactivity of various 5-substituted tetrazolium salts toward carbon nucleophiles depends on the nature of the substituents at C-5. With electronegative substituents, nucleophilic substitution proceeds at C-5, whereas electron-donating substituents direct the nucleophiles towards N-2 yielding ring-cleaved products.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260514
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